You can do it while you're doing other things, assuming your computer is fast enough to handle it.

My method was to go through our CDs and grab ones I knew had a bunch of stuff on them that I'd want and started there. The time to transfer from a CD to your computer is longer than from the computer to the iPod. At first, because I didn't have the hard drive space, I'd delete the songs from my computer after they were on my iPod, but I don't have to do that anymore.

When you pop in a CD, all the songs are checked. You uncheck the ones you don't want to download and click "import". It's that easy, at least with iTunes.

I love my iPod. I used it yesterday to listen to a Mugglenet podcast, which made me feel incredibly hip and very geeky at the same time.

Charles:

There actually are services that will rip your entire collection for you, usually for around $1 a disc. Yeah, that's $200 in your case, but time, as they say, is moolah. Up to you whether it's worth it.

See this PC World review of ripping services.

Note that one of them, iRip, will actually place the songs on an iPod they sell you. Other services will let you send your iPod and they'll place the songs. Of course, keep in mind if you do this, it's not easy to move the songs back over to a PC, unless you buy additional software. (And Apple does not support this officially.) Some of the companies that rip directly to an iPod or other player should be able to give you a disk (usually in DVD format) with all your songs ripped there as well.

The PC World story does a good job of laying out the pros/cons.

Dwight.

I kind of have the best of both worlds when it comes to something like this. I have a CD walkman that can play MP3s that are burned to a CD-R.

As you might suspect, the answer to your question depends on the speed of the CD drive on your computer, how fast your processor runs, and how much space you have on your hard drive. The typical song runs in the 3-4 Mb range.

My wife bought me a 4GB IPod mini for my birthday. I already had most of the songs I wanted loaded on to ITunes at my work computer so uploading them to the IPod took no time at all.
It took me about a week to fill up my ITunes bringing 10 to 20 CDs at a time and importing them while I did other work. As William says, it depends on the speed of your computer. I use an IMac G5 at work and it went very quickly.
I would not recommend paying to have a service import your music. I think that would be a waste of money.
The most time consuming thing you will find is just going through your collection and deciding which songs you want on your IPod. Mine holds 1,000 songs and that is plenty. But now everytime I find some new music I want to add I have to go through the list and decide what I can take off. But that is half the fun of it anyway.
What you are creating is your own personal radio station that only plays music that you want to hear. I love it.

A lot depends on the size of your collection. I'm reripping ours after a catastrophic hard drive fail (fried in a storm) and I'm at about 110 CDs in a couple of months later. As you know, that's not a big chunk of our collection.

A typical CD takes my above-average-but-not-blazing music server machine about 8 minutes to rip and compress, but that's using LAME alt-preset-fast-extreme because I want the quality.

If you do decide to go the digital route, I would suggest that you think about naming strategies (my car mp3 player, for example, sorts by directory, then by file name, so if I don't include a track # in the name, the songs are played out of original order, which is bothersome on some albums).

Also, pick yourself a quality encoder. LAME isn't the fastest encoder, but it produces really nice mp3s that are noticeably better than some of the faster encoders out there (as in, you can hear the difference with a decent set of headphones). Other people have their favorite encoders and can offer advice, I'm sure.

The last time I did a big batch of ripping, I made it through 50 CDs in 3 or 4 hours, using a single computer. When I was doing the bulk of my collection, I used two laptops side-by-side, and it went a bit faster. I can't do the "work on other stuff while ripping" method, because I'll get distracted by the other stuff, and three hours later I've ripped five CDs.

Of course, once you get your whole CD collection ripped, THEN its time to get it all tagged by MusicBrainz, and then you have to go through and rate all the songs...